


Pillow Talk Confessional

by MsCaptainWinchester (rons_pigwidgeon)



Series: Confessions of a Cam Boy and Timestamps [3]
Category: Supernatural
Genre: Age Difference, Anal Fingering, Anal Sex, Autofellatio (discussed), Blow Jobs, Bottom Dean, Camboy Dean, Coming Untouched, Daddy Kink, Dean Winchester Has a Panty Kink, Established Relationship, Kink Negotiation, M/M, Panty Kink, Pillow Talk, Praise Kink, Protective Castiel, Rimming, Size Kink, Size Queen Dean, Top Benny Lafitte, Vacation, Voyeur Castiel, Voyeurism, Yoga
Language: English
Status: Completed
Published: 2018-02-12
Updated: 2018-02-12
Packaged: 2019-03-17 04:15:10
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,544
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13651236
Author URL: https://archiveofourown.org/users/rons_pigwidgeon/pseuds/MsCaptainWinchester
Summary: Curled up in bed after a nice, long fuck is the best time to get Dean talking, and he’s not ashamed to admit it. When he confesses to Cas that he might be interested in hooking up with a viewer on cam, Cas is more than on board.





	Pillow Talk Confessional

**Author's Note:**

> Timestamp for [Confessions of a Cam Boy](http://archiveofourown.org/works/8654578). I've working on this since I posted the original story in 2016.
> 
> Thank you to traveling-riverside-dean for betaing for me! 
> 
> This is my last planned timestamp, but I've always loved writing this series. If you would like to see more, please send me your ideas! I can't guarantee that every one will get written, but I would love suggestions.

Curled up in bed after a nice, long fuck is the best time to get Dean talking, and he’s not ashamed to admit it. When he’s stretched out against Cas’ side with Cas’ soft fingers trailing up and down his back, that’s when he feels bravest—like he can say literally anything and Cas won’t judge him, won’t chastise him, won’t do anything at all except stroke his back and let him talk.

So Dean talks. “I want to start doing yoga so I can get bendy enough to suck my own dick.”

“There’s a hot yoga studio down the block,” Cas tells him in a hushed tone, fingers endlessly trailing. “We could go together. I’d love to fuck you still all sweaty and panting from class.”

And so, they start going to yoga classes together on Tuesday nights and sometimes, afterwards, Cas barely waits until the front door closes behind them before he has Dean bent in half with his shorts down just passed his ass. They’ve started keeping lube and condoms in the hall table to save time.

-

“I don’t think I want to go to grad school after all. Too much money to do what I already do now.”

“My brother’s bakery needs a brand re-design. You could do freelance.” Up and down, his hand strokes from shoulder blades to ass cheeks and back again.

Dean meets Gabriel the next week over Skype and is surprised at how drastically different from Cas he is, both physically and in personality. He’s friendlier than Dean expected, and it leaves Dean wondering why the two brothers aren’t closer. He and Gabriel end up hitting it off, and Dean’s first freelance gig goes off without a hitch.

-

“I think I’m in love with you.”

“I’ve been in love with you for a long time,” Cas replies with a fond little half-smile. Dean raises up on his hands to look at Cas, more surprised than he’ll admit to being.

“Yeah?”

“Mhmm,” Cas hums, smile widening. Dean can’t help but grin, giddiness fluttering in his belly as he leans down to kiss Cas. If they spend a half hour murmuring I-love-yous to each other between kisses, it’s no one’s business but their own.

-

“I think I want to meet up with CB or Morningstar or one of the other top viewers. Maybe have them on the cam? You could watch or I could suck you off while they fuck me?”

It’s the first time the fingers still. “I thought you weren’t interested in having a third.”

He had said that when Cas brought it up for the first time, months ago, but he’s a lot more secure in their relationship now. He raises up on his elbows over Cas to look him in the eyes. “I’ve been thinking I might like it, if it was one of the viewers.”

Cas smooths a thumb over Dean’s cheek, his touch soft but deliberate. “You know I enjoy the idea of watching another man giving you pleasure.” His expression turns serious, his eyebrow raising into a hard arch as he continues to stroke Dean’s cheek. “We would have to be very careful. I know they appear to be nice, friendly people who appreciate you, but the reality could be very different. You got lucky with me, but someone else could be a stalker or abusive or wish to do you or me harm in a fit of jealousy.”

“You’ve been talking to them as long as I have. You get the feeling someone like CB wants to hurt me?”

“I’m just saying that we should approach something like that with caution. Anyone we decided to meet would have to submit to a background check and—“

“Is that a thing we can do?”

“Of course. I would also want to meet them at least once in public prior to allowing them anywhere near you in private.”

“By yourself or with me?”

“Together, I think. If they do mean us harm, they’re less likely to do anything if there’s two of us.”

"I don't think any of them will hurt us, Cas.”

Cas lifts Dean’s chin up to make eye contact. “You are precious to me. Let me keep you safe.”

Dean softens to his tone and leans up to kiss him, little butterflies fluttering in his stomach at the touch even after almost a year together.

-

 **Cajunboy1872** is the subscriber they settle on. He was the first to respond to their request, and he didn’t have a problem with giving Cas the information needed for a background check—which came back mostly clean except for a few speeding tickets (for his fishing boat, and not his car, oddly enough). His name is Benny LaFitte, he’s 38, and he owns a little diner just north of New Orleans.

Dean has talked to him on the phone twice now and likes him more with each conversation. He’s down to do whatever Dean and Cas want, which is great, because Dean has a lot of ideas. They decide to take a weekend trip to visit, but have to wait a long while before they can go. Dean has never been happier that Sandover didn’t offer him a permanent position. He’s starting to think Cas might have an easier time finding a kidney donor than getting his boss to give him a couple of days of vacation.

They finally manage to secure some time and a flight down, and Dean is so buzzed with excitement that he isn’t even nervous on the flight.

When they get out of the car in front of the diner, Cas slides his hand in Dean’s and squeezes. Dean looks over, grinning. “Are you as excited as I am?”

“I’m starting to be,” Cas says with a smile, leaning over to kiss Dean.

They head into the restaurant, where Benny told them he’s running the kitchen until late afternoon. It’s as small as Benny described to them, but it has a lot of charm. It reminds Dean of the kinds of places his family used to eat at on road trips when he was a kid. There’s even a display case of pies that has his mouth watering immediately. Behind the display case is a tall bear of a man with a ginger beard, a black fisherman’s hat, and eyes almost as blue as Cas’.

“Well aren’t you just the sweetest sight I’ve seen all day. Come on in, have a seat,” he says in the deep Cajun drawl that Dean recognizes from their phone conversations.

Dean grins and tugs Cas over to the counter by his hand. “Hey Benny, nice place you’ve got here.”

“It’s not much, but it’s mine.” He shrugs, eyes darting around the place before settling back on Dean with a sparkle that makes Dean tingle down to his toes. He definitely wants this man to fuck him. “Take a seat. I wasn’t sure if I was gonna see ya’ll today or not. Can I make you somethin’?”

Dean and Cas take seats at the counter, and Dean has to look down to try to hide his blush. “Yeah, we got to our hotel and uh… got distracted.”

“The bed is very comfortable,” Cas says with a self-satisfied smirk that makes Dean’s blush worsen. He slides a hand into the back pocket of Dean’s jeans, leaning into him.

“I bet,” Benny says, and Dean looks up to see him watching them with a tiny smirk. He glances around at the other two customers, an elderly man picking at a sandwich on the other end of the counter and a young mother and her baby sitting at one of the five tables, not paying them any attention.

“Maybe you can see for yourself later,” Cas says, and the insinuations in his tone are not subtle. Dean looks over at him, surprised that Cas isn’t still on high alert for serial killer signs.

Benny licks his lips, eyeing them both up. “I’d like that very much.”

They chat some more, and Benny makes them some of the best crab cakes Dean has ever eaten. By the time pie rolls around, the place is empty save for the three of them, and Benny comes around the counter to sit with them and have a slice of his own.

When the first bite explodes with flavor in his mouth, Dean groans and slumps against Benny’s shoulder. “Please tell me you make these yourself.”

“I do, indeed.”

Dean leans further into his space and looks up at him with hooded eyes. “I am going to give you the best blowjob of your life after this,” he says.

Benny’s cheeks pink, and he slides a hand over Dean’s thigh with a cautious look over Dean’s shoulders at Cas. Cas watches them with a twinkle in his eyes.

-

Dean turns to look back at Benny as Cas closes the door of their hotel room behind them. “You ready?” he asks.

An easy grin spreads over Benny’s face as he nods. “Oh yeah.”

Dean glances over his shoulder at Cas, who has wandered over to the minibar to pour drinks. He doesn’t look to be having second thoughts. Dean was a little worried that he might when it came down to doing the actual deed.

Dean turns back to Benny and steps into his space, reaching up to curl his hands over Benny’s wide shoulders and feel their shape beneath his hands. Dean might have an inch or two on him, but Benny is built like a linebacker. Dean can’t wait to be underneath him. He leans closer for a kiss that Benny meets halfway. The first touch of those soft lips against his is like sinking into a warm blanket, only made better by the light scratch of beard. Dean finds himself whining against his lips, pressing against Benny as strong hands wrap around his waist and pull him in. Yoga has done wonders for toning his muscles, but it hasn’t added much bulk yet. In Benny’s arms, Dean feels every bit the twink he is, and he loves it.

As the kiss deepens, Dean can feel the press of Benny’s cock against his thigh and is more than pleased with the shape of it. He reaches down to cup the bulge in his hand, testing the girth through the worn fabric of Benny’s jeans. He pulls away breathless to look down at it in his hand. “Fuck, I can’t wait to get that in me,” he says, grinning.

He drops to his knees, too excited to see it to bother with patience. His hands travel down Benny’s thick torso to his button fly. He makes quick work of it, spreading the fabric apart and tugging it down to expose the fact that Benny wasn’t wearing underwear. He moans at the sight of the beautiful fat cock, bright pink and covered in thick veins. He’s not as long as Cas, but easily the girth of a coke can. Dean’s not even sure he’ll be able fit the whole thing in his mouth, but he’d be damned if he wasn’t going to try.

He has his tongue out, ready to lick along each of those gorgeous veins, when a condom packet is thrust in between him and his prize. He looks up to find Cas staring down at him with a look of patient warning, holding the condom out. Dean takes it and watches Cas lean into Benny’s side for a kiss of his own as he opens the foil with his teeth. It’s a bit of a surprise. Cas hadn’t seemed much interested in getting hands-on with Benny himself. Dean hadn’t even bothering imaginging what it might feel like to watch Cas kiss someone else, but now that he has had the pleasure, he wants to suck both of them off at once. He rolls the condom onto Benny’s shaft and takes the head into his mouth, suckling at it while he tries to get Cas’ pants open, too.

Cas pulls away with a tsking noise. “Not yet. Show Benny what you can do with that pretty mouth of yours,” he says, stroking a finger along Dean’s jaw while he traces the outline of Benny’s cock through Dean’s cheek. He steps away and disappears into the bedroom. Dean looks up at Benny and smiles around his mouthful at the awed look he’s getting back. He takes a firm grip of Benny’s cock and does exactly as Cas ordered.

Dean is inordinately pleased at how quickly he can get Benny to come, just from a few eye-batting looks and a few good sucks on his head. Benny grabs onto the back of his hair, thick fingers digging into Dean’s skin as he shudders through his orgasm, and the only disappointing part of watching him turn into a panting mess is that Dean isn’t covered in cum right now. He consoles himself by kissing the cum-filled condom before standing up to kiss the stunned look off Benny’s face.

“That was amazing, cher,” Benny rumbles against his lips, wrapping his arms around Dean’s waist and burying his face in Dean’s neck. Dean can’t keep the grin off his face, stroking Benny’s hair as he looks over Benny’s shoulder. Cas is spread out on the couch in just his boxers, drink in hand, watching them with the kind of heat that makes Dean want to crawl into his lap and never leave. Dean mouths a thank you for letting this happen, and Cas raises his drink in acknowledgement.

“Why don’t we have a drink and let Benny recover a little before we head into the bedroom?” Cas suggests, indicating the empty cushions next to him.

Dean pulls Benny over and sits him down, handing him one of the glasses Cas had waiting on the coffee table for them. Benny whistles long and low. “Castiel, you are one lucky son of a bitch,” he says, raising his glass to Cas in a cheer before taking a drink.

Dean laughs, grabbing his own drink and curling up in Cas’ lap the way he’d wanted to, kicking his shoes off and draping his feet over Benny’s lap to keep their connection. “You are kinda lucky, aren’t you?” he says, turning in Cas’ arms to kiss him.

Cas’ eyes darken as he grips the back of Dean’s neck, his look possessive. “I am beyond blessed.”

Dean’s smile gets bigger, starting to ache at the corners from over-use. He rubs his foot against Benny’s bare inner thigh. “I’m pretty lucky, too.” He lets Cas pull him into a kiss, his mouth whiskey sharp and warm.

Benny starts massaging up Dean’s calf, fingers digging in deep with every stroke of his hand. Dean curls his toes up under Benny’s balls and strokes him back, grinning against Cas’ mouth. It’s looking like he’s about to have one hell of a weekend.

-

“You said you’re fine with filming, correct?” Cas asks, SLR in hand as he sets up the tripod in the corner of the room.

“Didn’t know you were the cameraman, chief,” Benny says, leaning his hip against the bed as he watches Cas work. Dean circles to Benny's side of the bed, excited at the prospect of finally getting that fat cock inside him.

Cas’ mouth curls up in a smile, but his focus is on setting the camera up on the tripod. “Do you care if your face is on camera?”

“Nah. If anyone who knows me saw this, they wouldn’t show nobody, ‘cause then they’d have to admit to watching gay porn,” he says with a hint of humor as he pulls his shirt over his head to reveal a burly torso, muscular if not exactly chiseled. Dean licks his lips, reaching out to twist his fingers in the short hair covering his chest.

“I bet you could bench-press me. That is so hot,” he says, grinning as Benny pulls him into a kiss.

“Only one way to find out.” Benny scoops him up into his arms and lifts him over his head, nuzzling his nose into Dean’s crotch with a teasing noise. Dean starts laughing and doesn’t stop until Benny tosses him onto the bed.

He raises up on his elbows and twists around to get Cas’ reaction. Cas is smiling all gummy, standing next to the camera and the laptop propped up on a chair right next to the bed. Dean sits up and swerves around to wave at the camera, happy to see Cas already has his feed up. He’d almost forgotten they were planning to stream this. “Hey everyone, ready for our surprise?”

The chat fills up with affirmatives. Dean looks back at Benny, standing at the other end of the bed, and grins. “We have a guest today. Benny?”

Benny waves at the camera, a little blush pinking his ruddy cheeks. "Evening,” he says. Dean turns back to the camera, still grinning.

“You guys remember how I said Bee-man and I were going on a trip? We flew down to meet up with one of my long-time viewers. You all know Benny as Cajunboy1872.” The chat moves too fast to read for a minute, but then Dean catches snippets. “Oh yeah, we are,” he responds to someone asking if they’re planning to fuck. He reads a few comments accusing him of cheating and frowns. “Hey now, I would never do that to Bee-man. He’s right here with us, aren’t you, sir?”

Cas squints, clearly displeased with the suggestion that Dean would cheat on him. He waves a hand in front of the camera lens, but stays firmly behind it. “Dean has my full consent. I am quite looking forward to watching Benny take him apart.” The chat quickly agrees.

Dean huffs a laugh as he stretches out on the silky soft sheets, twisting around to face Benny again. “Think you can do that, big guy?”

Benny’s eyes hood over, and he grabs Dean’s calves, pulling him closer and leaning over to kiss him. “I got more plans for you than we got time in the world to get through.”

“Promises, promises,” Dean teases, reaching up for another kiss. Benny indulges him a little longer before patting him on the hip.

“Turn over, sugar,” he urges, running his hand up Dean’s bare side. Dean rolls onto his stomach in a lazy sprawl, humming at the appreciative noise Benny makes behind him and pushing his hips up looking for more praise. “So gorgeous,” Benny murmurs as his fingers trail down Dean’s bare back, his touch reverent. He snags Dean’s shorts, pulling them down his legs and gasping when he spies the mint green lace panties hiding underneath. The pants are gone in the next instant and Benny’s fingers are tracing the edges of the lace.

“Did you pick these out just for me?” Benny asks.

Dean grins at him over his shoulder, spreading his legs open to give Benny a better view. “Bee-man picked them out. You like?”

“They’re perfect. You’re perfect.” He leans over to press an earnest kiss to Dean’s lips. Dean hums into it, kicking his legs a little in happiness. When Benny pulls away again, his eyes are soft to match the warmth of his cheeks. Dean feels his heart flutter.

He looks up at Cas when Benny slinks back down his body to explore the panties. Cas is watching them with the same fixation he gets watching Dean try a new yoga pose. Dean smiles, unable to stop himself from blushing even as Benny tugs down the underwear and presses dry kisses to the cleft of Dean’s ass.

Dean’s eyes flutter closed when Benny’s tongue drags down between his cheeks, the scruff of his beard tickling Dean’s skin. The underwear is dragged all the way off, and Benny pushes his legs wide open, broad hands spreading his cheeks wide. Dean expects a tongue next, but the cold air greets him instead. He glances back to see Benny just looking, a thumb brushing over his pucker, a look of awe on his face.

“Isn’t he the most beautiful thing you’ve ever seen?” Cas asks, his voice gruff with lust.

“You really are, darlin’,” Benny tells him, brushing his thumb over Dean’s pucker again. A shiver shoots up Dean’s spine and he lifts his hips again, looking for more.

“Stop teasing me,” he says, grabbing a handful of the comforter. Benny lowers his head to tease his tongue against Dean’s hole, flickering it back and forth until Dean growls impatiently and pushes back against his mouth. Benny chuckles at him, a deep rumble that resonates through Dean, before the flat of his tongue strokes up Dean’s crack.

“Oh fuck…” Dean cries out, burying his face against his arm. He can feel Benny grin against his skin.

And then Benny proceeds to slowly and thoroughly take him to pieces with his tongue.

Dean is _not_ prepared. Not at _all_. There are tears trailing down his cheeks and his breaths are coming out in choked-off little whines by the time his orgasm washes over him. All the air slams out of him as he spills, untouched, all over the bed beneath him. Benny lifts his head up, the beard burn causing Dean’s skin to tingle pleasantly every time he moves. “Oh please, I can’t take it. Want that cock in me so bad, Benny.” Dean doesn’t even realize he’s been talking until Benny’s sitting up on his knees between Dean’s spread legs, reaching for the condom and bottle of lube Cas is holding out for him.

“Patience, darlin’, I got you.” Benny strokes a hand over his hip as Dean tries to pull himself back together, but his edges are too frayed. He barely manages to push his hips back against Benny’s hand.

Cold lube is drizzled over his hole and warmed up with two fat fingers sliding inside him, stretching him so good. “Oh fuck, Benny…” Dean whines, spreading his knees wider to give him more room. He is vaguely aware of Cas walking around to the side of the bed and looks behind him in time to watch Cas roll the condom down Benny’s shaft with a tight fist as they share a deep kiss. Dean has enough sense to worry about Cas being on screen, but when he looks up at the feed, Cas’ face is just out of frame.

Two fingers become three as Cas walks back around to the side of the camera, combing through Dean’s sweaty hair as he passes. Dean reaches out to link their fingers together, pulling Cas’ hand close enough to kiss. Benny’s fingers are pulling him apart in ways he didn’t even know were possible, and he needs the extra grounding before he floats away. Cas pets through his hair with the hand Dean hasn’t taken hostage.

“You’re doing so well, gorgeous. Are you ready for Benny’s cock?” Cas asks.

Dean makes an incomprehensible sound and nods, pressing his cheek to Cas’ wrist. Benny drops a kiss on his shoulder blade, another on his ear. “You’re taking my fingers like a champ, cher. You ready for the real thing?”

“Benny… please…” Dean manages, whining as the fingers slide out of him. The fat head of his cock rubs against his pucker next, teasing, pushing in just enough to leave him wanting more. Dean growls in frustration and gets his knees back underneath him so he can find some semblance of control. Benny follows him onto his knees, teasing. Too much teasing.

Dean waits until Benny has his head nestled right where Dean wants him and shoves his hips back, crying out as Benny’s thick shaft opens him wide. Benny grabs onto his hips to try to guide him gently, but Dean is not having any of that slow shit. Not after all the teasing and coaxing and praise. He wants Benny’s fat cock all the way to the hilt, and he doesn’t stop pushing until he gets what he wants.

“Oh fuck, Benny, you’re so big. You feel so fucking good stretching me wide open.” Benny pulls out just enough to make Dean feel it when he shoves back in, and Dean cries out again. He lets go of Cas’ hand so he can brace himself on the bed. He feels like he’s being split in two, like he’ll never be able to get this full again. He can barely function under the pleasure of it.

Benny drapes himself over Dean’s back, wrapping an arm around his neck, and starts pounding him for all he’s worth. Dean shouts, unable to keep the noises from spilling out as Benny batters his prostate. He can feel the tears trickling down the corners of his eyes and doesn’t even care about what he must look like. He clings to Benny’s arm with one hand, begging for more, harder, faster. He’s hard again and coming quick as a teenager, trembling against Benny’s constant, steady pounding inside him. It’s overwhelming, constant, unrelenting. He feels helpless to stop it and desperate for more all at once.

When Benny comes, it’s like riding a volcano. He shakes with it, grunting into Dean’s shoulder as his hips jerk erratically into Dean’s. He stutters to a stop after what feels like forever, panting through the smile Dean can feel pressed against his skin. When he pulls out, Dean twists around grinning and tugs him down for a kiss.

-

  
“We’ll see you tomorrow?” Dean grasps the edge of the door and leans into it as Benny passes him. He turns in the hallway with a wink.

“Bright and early. Think you’re gonna like the bayou.”

Dean thinks so, too. He glances down the hall before leaning over to kiss Benny on the cheek. Benny strokes a finger down his nose before walking off towards the elevators. Dean swings the door closed, sighing happily as he throws the bolt.

Cas is sprawled out half-under the sheets when Dean gets back into the bedroom, still limp-limbed and floppy from the blowjob Dean gave him after the camera turned off. Dean crawls up into Cas’ arms, dropping down between his spread legs and pressing a sloppy kiss to his chin before laying his head on Cas’ chest. “That was amazing. Thank you for letting me play.”

Cas strokes fingers through his hair with one hand while the other strokes up and down Dean’s arm. “It was my pleasure. Watching someone else worship you as well as I do was very satisfying.” He takes hold of Dean’s head and tilts his head up to meet his eyes. “You were so beautiful under his hands.”

Dean smiles up at him. “Watching me with someone else turn you on, daddy?”

Cas strokes his fingers over Dean’s cheek to drag his bottom lip down, his right leg twisting over Dean’s possessively. “You turn me on, now and always.”

Dean raises up on his hands and crawls the rest of the way up Cas’ body to kiss him, pleased when Cas rolls him onto his back and covers him with his body, their legs tangling. When Cas pulls back, Dean smiles up at him, warm and happy. “I love you,” he murmurs.

Cas kisses him again. It’s a long time before they go to sleep.

**Author's Note:**

> If you want writing updates from me, you can follow me on Twitter [@RonsPigwidgeon](https://twitter.com/RonsPigwidgeon) or Tumblr at [MsCaptainWinchester](https://mscaptainwinchester.tumblr.com/).


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